[ CAS No. 1187929-04-9 ] {[proInfo.proName]}

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Quality Control of [ 1187929-04-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1187929-04-9 ]

SDS Specification

Alternatived Products of [ 1187929-04-9 ]

Product Details of [ 1187929-04-9 ]

CAS No. :	1187929-04-9	MDL No. :	MFCD06809590
Formula :	C₅H₁₀ClNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CWSLARZELUGARZ-WCCKRBBISA-N
M.W :	167.59	Pubchem ID :	42614332
Synonyms :

Calculated chemistry of [ 1187929-04-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.57
TPSA :	58.56 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-9.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-2.43
Log Po/w (WLOGP) :	-0.52
Log Po/w (MLOGP) :	-3.07
Log Po/w (SILICOS-IT) :	-0.05
Consensus Log Po/w :	-1.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.72
Solubility :	875.0 mg/ml ; 5.22 mol/l
Class :	Highly soluble
Log S (Ali) :	1.74
Solubility :	9220.0 mg/ml ; 55.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	0.11
Solubility :	217.0 mg/ml ; 1.29 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.3

Safety of [ 1187929-04-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1187929-04-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1187929-04-9 ]

[ 1187929-04-9 ] Synthesis Path-Downstream 1~17

1
[ 1187929-04-9 ]
[ 28920-43-6 ]
[ 281655-37-6 ]

Reference： [1]Journal of Biological Chemistry,2010,vol. 285,p. 8976 - 8984

2
[ 1187929-04-9 ]
[ 1578155-69-7 ]
[ 1578153-27-1 ]

Yield	Reaction Conditions	Operation in experiment
1.01 kg	With 2,2,6,6-tetramethyl-piperidine; In dichloromethane; for 16.0h;Large scale;	The 50 L flask was charged with crude (4R)-6-(bromomethyl)-4-(2-chloro-4-fluoro- phenyl)-2-thiazol-2-yl- 1 ,4-dthydropyrimidine-5-carboxylic acid methyl ester(compound IXa) from last step) in dichloromethane solution, (35)-<strong>[1187929-04-9]morpholine-3-carboxylic acid hydrochloride</strong>salt (1.02 eq, 0.53 kg, 3.14 mol) and 2,2,6,6-tetramethylpiperidine (2.87 eq, 1.24 kg, 8.80 mol) at25C - 28 C. The resulting solution was stirred at 25 C - 28 C for 16 hours.After reaction completion, water (10.0 L) was added to reaction mixture to quench thereaction. The reaction mixture was adjusted to pH = 2.5 using H3P04. After phase separation, the organic phase was washed with acid solution (using H3P04 to adjust pH = 2.5) twice to remove all the TMP. The organic solution was concentrated to dryness in vacuo and the residue was redissolved in MIBK (10.0 L). To the solution was then added MSA (0.78 eq, 0.23 kg, 2.39 mol) slowly in 2 hours. After the addition of MSA, the solution was heated to 40 C - 45 C and stirred for 2 hours. The resulting suspension was cooled to 23 C - 25 C. The reaction mixture was filtered and the collected solid was rinsed with MIBK (1.0 L). The resulting solid was dried invacuum oven at 45 C for 16 hours to afford the MSA salt of Example 3 (1.45 kg).To a 20 L flask was charged with MSA salt of Example 3 (L45 kg, 2.45 mel), EtOAc (15.0 L) and NaHCO3 aqueous solution (10 wt%, L33 kg) at roomtemperature After phase separation, the organic phase was washed with water (3.0 L). The organic solution was concentrated to dryness in vacu.o and the residue was re-dissolved in acetone (1.10 L).The resulting acetone solution was slowly added into water (12,0 L) in 12 hours at 20C -25 C. The resulting suspension was stirred for an additional 72 hours at 20C -25 C. Reaction mixture was filtered and the collected solid was rinsed with water (5.0 L) for 2 times. The resulting solid was dried under vacuum at 55 C for 72 hours until the weight was constant to give 1.01 kg product as light yellow solid. The purity was 99.5%, the yield was 66.6% for 3 steps,and the MS m/e =495.1 [M+H].

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 3352 - 3371
[2]Patent: WO2016/102438,2016,A1 .Location in patent: Page/Page column 13; 14; 15; 16

3
[ 1187929-04-9 ]
(R)-4-(2-chlorophenyl)-6-bromomethyl-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester [ No CAS ]
(3S)-4-[[(4S)-4-(4-chlorophenyl)-5-methoxycarbonyl-2-thiazol-2-yl-1,4-dihydropyrimidin-6-yl]methyl]morpholine-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.40 g	With 2,2,6,6-tetramethyl-piperidine; In dichloromethane; at 25 - 28℃; for 16.0h;	To the 100 mL flask was charged with (R)-4-(2-chlorophenyl)-6-bromomethyl-2-thiazol- 2-yl-1,4-dthydropyrimidine-5-carboxylic acid ethyl ester (compound IXc, 8.14g, 18.50 mrnol) inDCM solution, (35)-<strong>[1187929-04-9]morpholine-3-carboxylic acid hydrochloride</strong> salt (compound X, 1.50 eq.,4.64 g, 27.70 mmol) and 2,2,6,6-tetramethylpiperidine (5.10 eq, 13.03 g, 94.16 mmoi), The reaction mixture was stirred at 25 C - 28 C for 16 hours. After reaction completion, the reaction mixture was adjusted to pH = 2.5 using H3P04, After phase separation, the organic phase was washed with acid water (using H3P04 to adjust to pH = 2.5) twice to remove all the TMP andconcentrated till dryness in vacuo. The residue was dissolved in EtOAc (30 mL) at 25 C -28 C. To the previous solution was then slowly added n-heptane (50 rnL) while maintain at 25 C -28C. The resulted suspension was stirred for another 0.5 hour at 25 C -28 C. After vacuum filtration, the collected solid was dried in vacuum oven at 55 C for 16 hours until the weight was constant to give 7.40 g product (Example 10) as a yellow solid. The purity was 99.0%, the yieldwas 80.7%, and MS m/e =49 1.3 [M+H] .

Reference： [1]Patent: WO2016/102438,2016,A1 .Location in patent: Page/Page column 23

4
[ 1187929-04-9 ]
(R)-6-(bromomethyl)-4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester [ No CAS ]
[ 1578153-81-7 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 3352 - 3371
[2]Journal of Medicinal Chemistry,2019

5
[ 1187929-04-9 ]
C₁₈H₁₆BrClFN₃O₂S [ No CAS ]
(3S)-4-[[4-(2-chloro-4-fluoro-phenyl)-5-propoxycarbonyl-2-thiazol-2-yl-1,4-dihydropyrimidin-6-yl]methyl]morpholine-3-carboxylic acid [ No CAS ]